Hydrochloric Acid → 4-Methylphenyl acetate

HRID 45426

Reaction equation

HRID 45426 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9](Cl)(=[O:11])[CH3:10].Cl>N1C=CC=CC=1>[CH3:8][C:3]1[CH:2]=[CH:1][C:6]([O:7][C:9]([CH3:10])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2879P-CresolHCID 6367Acetyl chloride

Product 1

HCID 87974-Methylphenyl acetateYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 65.0 g (0.60 mol) of p-cresol, 51.8 g (0.66 mol) of acetyl chloride, and 6 mL of anhydrous pyridine was refluxed for 1.5 h and then added to 600 mL of 2% hydrochloric acid. The product was extracted with 2×100 mL of diethyl ether, the combined extract was washed with 2% NaOH, then dried over Na2SO4, and evaporated to dryness. Drying the residue in vacuum gave 83.7 g (93%) of p-tolyl acetate (bp 104-105° C./25 mm Hg). A mixture of 40.0 g (0.27 mol) of p-tolyl acetate and 45.0 (0.34 mol) of AlCl3 was slowly heated to 120-125° C. for 30 min. The mixture was stirred for 1 hr and then 500 mL of 2M HCl was added at 0° C. The product was extracted with 3×100 mL of diethyl ether, the combined extract was dried over Na2SO4 and then evaporated to dryness. This gave 39.7 g (99%) of the title product which was further used without an additional purification.

Workup

  1. temperaturewas refluxed for 1.5 h
  2. extractionThe product was extracted with 2×100 mL of diethyl ether
  3. extractionthe combined extract
  4. washwas washed with 2% NaOH
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customDrying the residue in vacuum

Sources & evidence

ORD record
ord-c018954371ce43c689b66af69f2d5e77
Source dataset
uspto-grants-2013_09
Patent number
US08541521B2

Linked notes

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